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Former President Donald Trump has repeatedly expressed his desire to see critics investigated, exerting influence on the DOJ to prosecute ex FBI Director James Comey and New York Attorney General Letitia James.

"We can't delay any longer, it's damaging our reputation and credibility," the president stated last month in a social media post.

"I was impeached twice, and indicted me (five times!)" he said, mentioning the multiple legal proceedings he encountered after departing the White House in 2021 and James's civil case.

Each have since been charged, in cases that many specialists have stated seem to be driven by politics and challenging to succeed in legal proceedings.

But the latest charges against a presidential opponent, ex security advisor John Bolton, differ significantly, legal specialists and former prosecutors say.

"In my opinion, contrasting Bolton's charges to James' is like comparing two different things," said Mark Lesko, a ex federal prosecutor for the Eastern District of New York.

The Specifics of Bolton's Case

Bolton has been formally charged on federal charges related to the supposed improper handling of sensitive materials. Since departing the White House in 2019, he has emerged as a outspoken presidential opponent, going so far as to describe him "stunningly uninformed" and unfit for office in his memoir.

Experts contend that while there may be political reasons to go after Bolton, the procedures used to obtain an charge and the proof compiled against him indicate a potentially stronger case than the Justice Department brought against James.

"This misconduct that's being claimed is simultaneously more serious and seems to have occurred over a considerable period of time," commented Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

Throughout his tenure as Trump's national security adviser, and following his 2019 White House departure, authorities alleged that Bolton put the country at risk by improperly keeping and transmitting classified information to relatives using unprotected methods, including AOL. Several of the materials were marked highly classified.

The charge states that at a certain time a unauthorized user accessed to Bolton's account where documents were stored and sent an apparent warning to cause "the largest controversy since Hillary [Clinton]'s emails were released".

Bolton pleaded not guilty during a court appearance on Friday to eighteen separate counts of mishandling classified information.

Political Motivation or a Substantial Case?

The schedule of his charge - arriving on the tails of allegations against Comey - has renewed questions about political pressure on the legal system.

Trump once suggested Bolton should be in prison, and described him a "disreputable person". Bolton, for his role, wrote a book about his time in the Trump government that was sharply negative of the leader.

"There's no question that the timing of this charge, when paired with others, has raised doubts about the strength of these charges, and why these charges are being brought at this time," stated Jamil Jaffer, founder and executive director of the National Security Institute.

Nevertheless, he continued, "should the Justice Department is able to demonstrate the allegations alleged and show the material is properly designated, his conduct may very well have violated the law".

Charging such a high-ranking figure for improperly handling classified documents is "uncommon" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Situations that involve classified information present difficulties to prosecute, but they may and are brought against both low-level and senior officials, from time to time," she said.

Similarities to Investigations into Former President and Biden

Trump similarly encountered allegations of wrongfully storing classified documents at his Mar-a-Lago property in Florida and hindering their recovery, but that matter was ultimately dismissed by a federal judge and voided by his re-election as leader.

A special counsel also found that former President Joe Biden wrongfully maintained sensitive materials from his period as vice president, but did not criminally charge him.

Bolton's situation bears similarities to Trump's classified documents matters, noted Mr Lesko, who also held a top security role at the DOJ.

Strict procedures govern the handling of classified documents. To win a guilty verdict, the prosecution must prove that Bolton knew the material he was transmitting was classified, and he had to intentionally transmit it to someone not entitled to receive it.

"Due to the classified nature of the material at question in this matter, we lack a lot of details about the reasons the prosecution contends elements like the diary entries and the additional information he shared by email, and why there were classified," explained Mr Jaffer.

A More Conventional Prosecution

The procedure by which the Justice Department brought this case will be under scrutiny, following Trump openly expressed his wish to see his critics charged and several of those indictments came to fruition.

But Mr Lesko indicated in Bolton's case, authorities seem to have followed protocol.

"This Bolton prosecution and eventually the indictment appeared to have followed the regular process including the rules and standards within the Department of Justice," he said.

In contrast to Comey's short, two-page charge, Bolton's was a increasingly "conventional" filing that "explicitly outlines the details concerning the circumstances and situation here," Mr Lesko commented.

"It seems reasonably consistent with a series of precedents... where public servants improperly handled and shared sensitive information."